Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport ability, light-emitting ability, and thermal stability; and an organic electroluminescent device comprising same in one or more organic layers, thereby having properties such as luminous efficiency, driving voltage and lifetime that are improved.

Description

Organic compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0005] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0006] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0007] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0008] [Prior Art Literature]

[0009] [Patent Literature]

[0010] Republic of Korea Published Patent No. 10-2020-0118188

[0011]

[0012] The present invention has a technical objective of providing a novel compound that has excellent electron injection and transport capabilities, luminescence capabilities, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material.

[0013] In addition, the present invention has another technical objective of providing an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, comprising the aforementioned novel compound.

[0014] Other objects and advantages of the present invention may be more clearly explained by the following detailed description of the invention and claims.

[0015]

[0016] To achieve the above-mentioned technical problem, the present invention provides a compound represented by the following chemical formula 1.

[0017] [Chemical Formula 1]

[0018]

[0019] In the above chemical formula 1,

[0020] A plurality of Xs are identical or different from one another, and each is independently CR5 or N, provided that at least two of the plurality of Xs are N,

[0021] Ar1 consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 s's one-person diary, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei,

[0022] However, if Ar1 is a carbazole group, a structure in which the N of the carbazole group is directly bonded to the X-containing ring is excluded, and

[0023] L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei,

[0024] m and n are each independently integers from 0 to 3, and

[0025] R1 to R4 are identical or different from each other, and each independently C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group;

[0026] R5 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei;

[0027] a to c are each independently integers from 0 to 5, and h is an integer from 0 to 4, provided that a+b+c+h ≥ 1, and

[0028] R 11 to R 14 The elements are identical or different from each other and are each independently selected from the group consisting of deuterium (D), halogen, and cyano group, and

[0029] d is an integer from 0 to 4, and e to g are each independently integers from 0 to 5, and

[0030] The arylene group and heteroarylene group of L1 to L2 above; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group of Ar1 and R5 above; The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of the above R1~R4 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0031] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0032] Here, the organic layer comprising the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0033]

[0034] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0035] In particular, when a compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional electron transport materials.

[0036] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0037] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0038]

[0039] The present invention will be described in detail below.

[0040] <New Organic Compounds>

[0041] According to the present invention, the compound represented by Formula 1 comprises two silane moietyes (e.g., tetraphenylsilane) centered around a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) and has a basic skeletal structure in which they are directly connected or connected through a separate linker (e.g., L1-L2), and is characterized by having an asymmetric structure as two different silane moietyes are introduced.

[0042] Specifically, the compound of Chemical Formula 1 contains two silane moiety groups with electron donor (EDG) characteristics and a nitrogen-containing aromatic ring (e.g., pyrimidine, triazine), which is a type of electron-withdrawing (EWG) group with high electron absorption. By introducing an azine group, which is a functional group with strong electron-withdrawing ability (EWG), the electron mobility is improved, thereby enabling the device to possess physicochemical properties more suitable for electron injection and electron transport. When the compound of Chemical Formula 1 described above is applied as a material for an electron transport layer or an electron transport auxiliary layer, electrons from the cathode can be effectively accepted, allowing for smooth electron transfer to the light-emitting layer. Consequently, this enables a reduction in the driving voltage of the device, leading to high efficiency and a long lifespan. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0043] In addition, the two silane moiety (e.g., tetraphenylsilane) included in the compound of Chemical Formula 1 above has a high triplet energy (T1) value through steric hindrance, so it can prevent excitons generated in the emissive layer from diffusing into the electron transport layer or hole transport layer adjacent to the emissive layer. Furthermore, the number of excitons contributing to light emission within the emissive layer is increased, thereby improving the luminous efficiency of the device, and the durability and stability of the device are enhanced, allowing the device lifespan to be efficiently increased. Moreover, by introducing two silane moietys, the low glass transition temperature (Tg) of conventional silane compounds can be overcome, and a glass transition temperature (Tg) of 120°C or higher can be secured, thereby significantly improving heat resistance.

[0044] Furthermore, the compound represented by Chemical Formula 1 above not only forms asymmetric molecular structure by including two different silane moieties, but also possesses bulkiness and is highly advantageous for electron transport by substituting the aryl group within one of the two silane moieties with various substituents (e.g., aryl, heteroaryl, cycloalkyl, alkyl, etc.), exhibiting characteristics of low driving voltage, high efficiency, and long lifespan. The excellent electron transport capability of this compound allows for high efficiency and rapid mobility during organic electroluminescence irradiation, and facilitates the control of HOMO and LUMO energy levels depending on the direction or position of the substituents. Therefore, an organic electroluminescent device using the above compound can exhibit high electron transport capability.

[0045] Meanwhile, the red and green light-emitting layers of organic electroluminescent devices utilize phosphorescent materials, and their technological maturity is currently high. In contrast, the blue light-emitting layer consists of fluorescent and phosphorescent materials; however, the fluorescent material requires performance improvement, and the blue phosphorescent material is still under development, resulting in a high barrier to entry. In other words, while the blue light-emitting layer has great potential for development, the technical difficulty is relatively high, which limits the ability to improve the performance (e.g., driving voltage, efficiency, lifespan, etc.) of blue organic light-emitting devices equipped with it. Accordingly, in the present invention, the compound of Chemical Formula 1 can be applied as an electron transport layer (ETL) or an electron transport auxiliary layer material in addition to the light-emitting layer (EML). Thus, there is an advantage in that the performance of the light-emitting layer, specifically the blue light-emitting layer, and the performance of the organic electroluminescent device equipped with it can be improved by changing the material of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic electroluminescent device.

[0046] According to the present invention, the compound represented by Formula 1 comprises a nitrogen-containing heteroaromatic ring with excellent electron transport capacity and EWG characteristics (e.g., azine, X-containing ring) and two distinct silane moietyes (e.g., tetraphenylsilane), and has a basic skeletal structure in which they are directly connected or connected through separate linkers (e.g., L1 to L2).

[0047] The above nitrogen-containing heterocyclic ring (e.g., X-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. In one example of a nitrogen-containing heteroaromatic ring, X may be identical or different from each other, and each may independently be CR5 or N, provided that at least two of the plurality of Xs contain N. By including a heterocyclic ring containing two or three nitrogen atoms in this way, superior electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

[0048] Here, R5 are identical or different from each other and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple R5s, the multiple R5s may be identical or different from each other. Specifically, R5 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0049] For example, a nitrogen-containing heterocyclic ring (e.g., a ring containing X) may be further specified by any one selected from the following structural formulas. However, it is not limited thereto.

[0050]

[0051] In the above formula,

[0052] * indicates the part connected to the above chemical formula 1, and

[0053] Ar1 is as defined in Chemical Formula 1.

[0054] In the above nitrogen-containing heterocyclic rings (e.g., X-containing rings), Ar1 can be substituted as various substituents. Ar1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar1 is C1~C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 The alkyl group, aryl group, heteroaryl group and arylsilyl group of Ar1 are each independently selected from the group consisting of arylsilyl groups, wherein the alkyl group, aryl group, heteroaryl group and arylsilyl group of Ar1 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In this case, when Ar1 is a carbazole group, a structure in which the N and X-containing ring of the carbazole group are directly bonded is excluded.

[0055] For example, Ar1 may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0056]

[0057]

[0058] In the above formula,

[0059] * indicates the part connected to the above chemical formula 1, and

[0060] R 21 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, at least one substituent known in the art (e.g., identical to the R5 definition excluding hydrogen) that is not indicated in the aforementioned structural formula may be substituted.

[0061] In the compound represented by Formula 1 according to the present invention, two distinct silane moietyes are included on both sides of the nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring). These two silane moietyes form an asymmetric structure with respect to the long axis of the molecule.

[0062] One of the two silane moietyes (e.g., a silane moiety containing R1 to R4) is substituted with at least one of the aryl groups contained in the moiety with various substituents (e.g., aryl, heteroaryl, cycloalkyl, alkyl, etc.) to have bulkiness, which is highly advantageous for electron transport, and to enable low driving voltage, high efficiency, and long lifespan characteristics.

[0063] R1 to R4 introduced into one of the two silane moietyes above are identical or different from each other, and each independently C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60It may form a condensation ring by combining with any adjacent group selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, R1 to R4 may be identical or different from each other, and each independently C1 to C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can form a condensation ring by combining with any adjacent group selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0064] Here, the condensation ring (condensation ring) may be selected from the group consisting of a single or polycyclic alicyclic ring, a single or polycyclic heteroalicyclic ring, a single or polycyclic aromatic ring, or a single or polycyclic heteroaromatic ring. Specifically, C6~C 24 It is preferable that it be an aromatic ring, or a heteroaromatic ring having 5 to 24 nuclei. However, a condensed ring structure formed by the condensation and / or fusion of R1 and R2, or R1 and R3, connected to two adjacent phenyls in a tetraphenylsilane moiety, such as the 9,9-diphenyl-9-silafluorene structure, is excluded.

[0065] The number of substituents R1 to R4 is not particularly limited. For example, a to c are each independently integers from 0 to 5, and h is an integer from 0 to 4, provided that a+b+c+h ≥ 1. Specifically, a to d are each integers from 0 to 3, and a+b+c+h ≥ 1. Here, if a is 0, R1 is a hydrogen, and if a is 1 to 5, R1 may have the aforementioned substituents. Also, the same applies to b and R2, c and R3, and h and R4.

[0066] For example, at least one of R1 to R4 that does not form a condensation ring may have any one substituent selected from the following structural formulas. However, it is not limited thereto.

[0067]

[0068]

[0069] In the above formula,

[0070] * indicates the part connected to the above chemical formula 1, and

[0071] R 22 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0072] Furthermore, since substituents such as aryl, heteroaryl, cycloalkyl, and alkyl groups are not introduced into the other of the two silane moietyes, an asymmetric structure is formed in terms of molecular structure. R introduced into this silane moiety 11 to R 14 The groups are identical or different from each other and are each independently selected from the group consisting of deuterium (D), halogen, and cyano group.

[0073] d is an integer from 0 to 4, and e to g are each independently integers from 0 to 5. Here, when d is 0, R 11 is hydrogen, and when d is 1 to 4, R 11 It may have the aforementioned substituents excluding hydrogen, such as deuterium (D), halogens, and cyano groups. In addition, e and R 12 , f and R 13 , g and R 14 It can also be applied in the same way.

[0074] In the compound represented by Formula 1 according to the present invention, a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) and two silane moietyes may be directly bonded or bonded through separate linkers (L1-L2). When separate linkers (L1-L2) exist between the nitrogen-containing heteroaromatic ring and the two silane moietyes, the HOMO region is expanded to provide a benefit to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO. In addition, by controlling the bonding position between the silane moiety and the linker, additional steric hindrance of the molecular structure can be generated, thereby inducing delocalization of LUMO orbitals and allowing for the control of LUMO values ​​suitable for an electron transport layer or an electron transport auxiliary layer.

[0075] These linkers (L1-L2) may be conventional divalent group linkers known in the art. Specifically, L1 and L2 may be identical or different from each other, and each may independently be a single bond or C6~C 24 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei.

[0076] m and n are integers from 0 to 3. Here, when n is 0, L1 is a single bond (direct bond), and when n is 1 to 3, it may have one or more selected from the group consisting of the aforementioned arylene group and heteroarylene group. Also, m and L2 may be applied in the same way. In this case, if there are multiple L1 or L2, the multiple L1 and L2 may be identical or different from each other.

[0077] Specific examples of the above-mentioned arylene group linker include phenylene groups, biphenylene groups, naphthylene groups, anthracenylene groups, indenylene groups, or pyrantrenylene groups. More specifically, it is preferable that it be a phenylene group or a biphenylene group.

[0078] In addition, specific examples of heteroarylene linkers include pyrrole moiety, furan moiety, thiophene moiety, pyridine moiety, pyrimidine moiety, pyrazine moiety, triazine moiety, dibenzofuran moiety, dibenzothiophene moiety, dibenzoselenophenone moiety, carbazolilene group, thiophenylene group, indolylene group, furinilene group, quinolinylene group, pyrroleylene group, imidazolilene group, oxazolilene group, or thiazolilene group.

[0079] For example, L1 and L2 may be identical or different from each other, and each may be independently a single bond or embodied in any one selected from the following structural formulas. However, this is not limited thereto.

[0080]

[0081] In the above formula,

[0082] * indicates the part connected to the above chemical formula 1, and

[0083] R 23 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, although not indicated in the aforementioned structural formula, at least one substituent known in the art, such as a substituent identical to the R5 definition part excluding hydrogen, may be substituted.

[0084] In the aforementioned Chemical Formula 1, the arylene group and heteroarylene group of L1 to L2; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group of Ar1 and R5; The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of the above R1~R4 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0085] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 2 to 5 below, depending on the type of nitrogen-containing heteroaromatic ring (e.g., X-containing ring). However, it is not limited thereto.

[0086] [Chemical Formula 2]

[0087]

[0088] [Chemical Formula 3]

[0089]

[0090] [Chemical Formula 4]

[0091]

[0092] [Chemical Formula 5]

[0093]

[0094] In the above formula,

[0095] Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each defined in Chemical Formula 1.

[0096] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 6 to 12 below, depending on the form of the R1 to R4 substituent introduced into one of the diarylsilane groups. However, it is not limited thereto.

[0097] [Chemical Formula 6]

[0098]

[0099] [Chemical Formula 7]

[0100]

[0101] [Chemical Formula 8]

[0102]

[0103] [Chemical Formula 9]

[0104]

[0105] [Chemical Formula 10]

[0106]

[0107] [Chemical Formula 11]

[0108]

[0109] [Chemical Formula 12]

[0110]

[0111] In the above formula,

[0112] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, provided that cases where a to c and h are each 0 are excluded.

[0113] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 13 to 18 below, depending on the bonding position of linker L1 or L2 located between the diarylsilane group and the azine group. However, it is not limited thereto.

[0114] [Chemical Formula 13]

[0115]

[0116] [Chemical Formula 14]

[0117]

[0118] [Chemical Formula 15]

[0119]

[0120] [Chemical Formula 16]

[0121]

[0122] [Chemical Formula 17]

[0123]

[0124] [Chemical Formula 18]

[0125]

[0126] In the above formula,

[0127] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each defined in Chemical Formula 1.

[0128] For a preferred specific example, the compound represented by the above formula 1 may be further embodied in any one of the following formulas 13A to 21A depending on the bonding positions of linkers L1 and L2 located between the diarylsilane group and the azine group.

[0129] [Chemical Formula 13A]

[0130]

[0131] [Chemical Formula 14A]

[0132]

[0133] [Chemical Formula 15A]

[0134]

[0135] [Chemical Formula 16A]

[0136]

[0137] [Chemical Formula 17A]

[0138]

[0139] [Chemical Formula 18A]

[0140]

[0141] [Chemical Formula 19A]

[0142]

[0143] [Chemical Formula 20A]

[0144]

[0145] [Chemical Formula 21A]

[0146]

[0147] In the above formula,

[0148] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each defined in Chemical Formula 1.

[0149] In another embodiment of the present invention, the compound represented by Formula 1 may be further specified by Formulas 19 to 27 below depending on the type of linker (e.g., L1-L2). However, it is not limited thereto.

[0150] [Chemical Formula 19]

[0151]

[0152] [Chemical Formula 20]

[0153]

[0154] [Chemical Formula 21]

[0155]

[0156] [Chemical Formula 22]

[0157]

[0158] [Chemical Formula 23]

[0159]

[0160] [Chemical Formula 24]

[0161]

[0162] [Chemical Formula 25]

[0163]

[0164] [Chemical Formula 26]

[0165]

[0166] [Chemical Formula 27]

[0167]

[0168] In the above formula,

[0169] X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and

[0170] Y1 and Y2 are identical or different from each other, and each independently O, S, NR 31 , and CR 32 R 33 It is selected from a group consisting of,

[0171] R 31 to R 33 They are identical or different from each other, and each independently hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei,

[0172] Rings A1 and A2 are identical or different from each other and are each independently condensed polycyclic aromatic rings having 8 to 18 carbon atoms.

[0173] As another embodiment of the present invention, the compound represented by Formula 1 may be further specified by Formulas 28 to 30 below depending on the type of condensation ring introduced into at least one of R1 to R3. However, it is not limited thereto.

[0174] [Chemical Formula 28]

[0175]

[0176] [Chemical Formula 29]

[0177]

[0178] [Chemical Formula 30]

[0179]

[0180] In the above formula,

[0181] X, Ar1, R 2~ R4, R 11 ~R 14 , b, c, d, e, f, g, h, m, and n are each defined as in Chemical Formula 1. For example, in the case of Chemical Formulas 28 to 30 above, since R1 combines with any adjacent group to form a condensed ring, it means that a has an integer greater than or equal to 1, even if not indicated in the formula. Also, if R2 to R4 form a condensed ring, b, c, and h can be applied in the same way.

[0182] Ring B is a condensed aromatic ring of monocyclic or polycyclic form having 6 to 18 carbon atoms, specifically a condensed polycyclic aromatic ring having 8 to 18 carbon atoms.

[0183] Ring C is a cycloalkyl group or an adamantane group having 3 to 12 carbon atoms, and

[0184] Z is O, S, NR 31 , and CR 32 R 33 It is selected from a group composed of,

[0185] R 31 to R 33 Each independently consists of hydrogen, deuterium, and C1~C 20 alkyl group of, C6~C 20 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 20 nuclei.

[0186] For a preferred specific example, the compound represented by the above chemical formulas 30 to 31 may be further embodied in any one of the following chemical formulas 29A to 30D.

[0187] [Chemical Formula 29A]

[0188]

[0189] [Chemical Formula 29B]

[0190]

[0191] [Chemical Formula 29C]

[0192]

[0193] [Chemical Formula 29D]

[0194]

[0195] [Chemical Formula 30A]

[0196]

[0197] [Chemical Formula 30B]

[0198]

[0199] [Chemical Formula 30C]

[0200]

[0201] [Chemical Formula 30D]

[0202]

[0203] In the above formula,

[0204] X, Ar1, R 2~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and

[0205] R 31 to R 33 Each is as defined in chemical formulas 30-31.

[0206] The compound represented by Formula 1 according to the present invention described above may be further embodied as a compound represented by any one of the compounds 1 to 192 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0216] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0217] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0218] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0219] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply attached (penant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0220] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0221] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0222] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0223] In the present invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0224] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0225] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0226] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0227] In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0228]

[0229] Electron Transport Layer Material

[0230] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0231] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0232] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0233] Electron transport layer materials that can be mixed with the compound of Formula 1 above include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used individually or in combination of two or more types.

[0234] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0235]

[0236] Electron Transport Auxiliary Layer Material

[0237] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0238] The above electron transport auxiliary layer is positioned between the light-emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0239] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport materials known in the art. Preferably, it is used alone.

[0240] Electron transport materials that can be mixed with the compound of Chemical Formula 1 above include electron transport materials commonly known in the art. Examples may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0241] In the present invention, when the compound of Formula 1 and the electron transport material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0242]

[0243] Organic Electroluminescent Device

[0244] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0245] Specifically, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0246] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising the compound of Chemical Formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifespan improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0247] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0248] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0249] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, the light-emitting layer, more preferably, the phosphorescent host may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0250] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0251] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more of the aforementioned organic layers comprise a compound represented by Chemical Formula 1.

[0252] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0253] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0254] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0255] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0256] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0257]

[0258] The present invention will be explained in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0259] [Preparation Examples 1 ~ 9]

[0260] [Preparation Example 1] - Synthesis of Compound Core 1

[0261]

[0262] 100 g (442.4 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 245.5 g (530.8 mmol) of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 425.6 g (22.1 mmol) of Pd(PPh3), and 122.3 g (884.7 mmol) of K2CO3 were added to 800 ml of THF and 200 ml of H2O and heated and stirred under reflux for 6 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 100.5 g (yield 43.2%) of compound Core 1.

[0263] Mass : [(M+H) + ] : 525

[0264]

[0265] [Preparation Example 2] - Synthesis of Compound Core 2

[0266]

[0267] Compound Core 2 was prepared in the same manner as in Preparation Example 1, except that 100 g (444.3 mmol) of 4,6-dichloro-2-phenylpyrimidine, 246.6 g (533.2 mmol) of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 425.7 g (22.2 mmol) of Pd(PPh3), 122.8 g (884.6 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the materials used in Preparation Example 1, to obtain 111.3 g (yield 47.7%) of compound Core 2.

[0268] Mass : [(M+H) + ] : 525

[0269]

[0270] [Preparation Example 3] - Synthesis of Compound Core 3

[0271]

[0272] The procedure was carried out in the same manner as in Preparation Example 1, except that 100 g (442.4 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 245.5 g (530.8 mmol) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 425.6 g (22.1 mmol) of Pd(PPh3), 122.3 g (884.7 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the materials used in Preparation Example 1, to obtain 121.7 g (yield 52.3%) of compound Core.

[0273] Mass : [(M+H) + ] : 525

[0274]

[0275] [Preparation Example 4] - Synthesis of Compound Core 4

[0276]

[0277] The procedure was carried out in the same manner as in Preparation Example 1, except that 100 g (444.3 mmol) of 4,6-dichloro-2-phenylpyrimidine, 246.6 g (533.2 mmol) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 425.7 g (22.2 mmol) of Pd(PPh3), 122.8 g (888.6 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the materials used in Preparation Example 1, to obtain 109.2 g (yield 46.8%) of compound Core.

[0278] Mass : [(M+H) + ] : 525

[0279]

[0280] [Preparation Example 5] - Synthesis of Compound Core 5

[0281]

[0282] Compound Core 3 was prepared in the same manner as in Preparation Example 1, except that 100 g (442.4 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 201.9 g (530.8 mmol) of (2-(triphenylsilyl)phenyl)boronic acid, 425.6 g (22.1 mmol) of Pd(PPh3), 122.3 g (884.7 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the substances used in Preparation Example 1, to obtain 96.1 g (yield 41.3%) of Core 3.

[0283] Mass : [(M+H) + ] : 525

[0284]

[0285] [Preparation Example 6] - Synthesis of Compound Core 6

[0286]

[0287] Compound Core 6 was prepared in the same manner as in Preparation Example 1, except that 100 g (442 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 258.8 g (530.8 mmol) of 4-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl) benzonitrile, 425.6 g (22.1 mmol) of Pd(PPh3), 122.3 g (884.7 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the materials used in Preparation Example 1, to obtain 135.3 g (yield 55.5%).

[0288] Mass : [(M+H) + ] : 550

[0289]

[0290] [Preparation Example 7] - Synthesis of Compound Core 7

[0291]

[0292] Compound Core 7 was prepared in the same manner as in Preparation Example 1, except that 100 g (316.3 mmol) of 2,4-dichloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine, 175.5 g (379.6 mmol) of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 418.3 g (15.8 mmol) of Pd(PPh3), 87.4 g (632.6 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the substances used in Preparation Example 1, to obtain 108.6 g (yield 55.7%).

[0293] Mass : [(M+H) + ] : 615

[0294]

[0295] [Preparation Example 8] - Synthesis of Compound Core 8

[0296]

[0297] Compound Core 8 was prepared in the same manner as in Preparation Example 1, except that 100 g (331 mmol) of 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, 183.7 g (397.1 mmol) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 419.1 g (16.5 mmol) of Pd(PPh3), 91.5 g (661.9 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the substances used in Preparation Example 1, to obtain 99.3 g (yield 49.8%).

[0298] Mass : [(M+H) + ] : 601

[0299]

[0300] [Preparation Example 9] - Synthesis of Compound Core 9

[0301]

[0302] Compound Core 9 was prepared in the same manner as in Preparation Example 1, except that 100 g (331 mmol) of 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine, 183.7 g (397.1 mmol) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 419.1 g (16.5 mmol) of Pd(PPh3), 91.5 g (661.9 mmol) of K2CO3, 800 ml of THF, and 200 ml of H2O were used instead of the substances used in Preparation Example 1, to obtain 100.4 g (yield 50.4%).

[0303] Mass : [(M+H) + ] : 601

[0304]

[0305] [Synthesized Examples 1 ~ 29]

[0306] [Synthesization Example 1] Synthesis of Compound 2

[0307]

[0308] 20.0 g (1 eq, 38.0 mmol) of Compound Core1 from [Preparation Example 1], 24.6 g (1.2 eq, 45.6 mmol) of [1,1'-biphenyl]-3-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane), 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were added to 800 ml of THF and 200 ml of H2O and heated and stirred under reflux for 6 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane, then the solid was filtered and dried to obtain 26.4 g (yield 77.0%) of compound 2.

[0309] Mass : [(M+H) + ] : 901

[0310]

[0311] [Synthesization Example 2] Synthesis of Compound 5

[0312]

[0313] Compound 5 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Compound Core 1 of [Preparation Example 1], 28.0 g (1.2 eq, 45.6 mmol) of [1,1':3',1''-terphenyl]-5'-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 20.1 g (yield 67.2%) of Compound 5.

[0314] Mass : [(M+H) + ] : 977

[0315]

[0316] [Synthesization Example 3] Synthesis of Compound 12

[0317]

[0318] Compound 12 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.1 mmol) of Core 2 of [Preparation Example 2], 28.1 g (1.2 eq, 45.7 mmol) of di([1,1'-biphenyl]-3-yl)(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.2 mmol) of K2CO3 were used with 800 ml of THF and 200 ml of H2O, respectively, to obtain 26.6 g (yield 71.5%) of compound 12.

[0319] Mass : [(M+H) + ] : 977

[0320]

[0321] [Synthesization Example 4] Synthesis of Compound 18

[0322]

[0323] Compound 18 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Compound 1 of [Preparation Example 1], 31.5 g (1.2 eq, 45.6 mmol) of tri([1,1'-biphenyl]-3-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 23.1 g (yield 57.6%) of Compound 18.

[0324] Mass : [(M+H) + ] : 1053

[0325]

[0326] [Synthesization Example 5] Synthesis of Compound 23

[0327]

[0328] Compound 23 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.1 mmol) of Core 2 of [Preparation Example 2], 31.6 g (1.2 eq, 45.7 mmol) of [1,1'-biphenyl]-2-yl([1,1'-biphenyl]-3-yl)([1,1'-biphenyl]-4-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.2 mmol) of K2CO3 were used with 800 ml of THF and 200 ml of H2O, respectively, to obtain 22.4 g (yield 55.8%) of compound 23.

[0329] Mass : [(M+H) + ] : 1053

[0330]

[0331] [Synthesization Example 6] Synthesis of Compound 27

[0332]

[0333] Compound 27 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol [1,1':2',1''-terphenyl]-4'-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 23.1 g (yield 62.2%) of compound 27.

[0334] Mass : [(M+H) + ] : 977

[0335]

[0336] [Synthesization Example 7] Synthesis of Compound 32

[0337]

[0338] Compound 32 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Core 3 of [Preparation Example 3], 28.0 g (1.2 eq, 45.6 mmol) of di([1,1'-biphenyl]-4-yl)(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 22.0 g (yield 59.3%) of compound 32.

[0339] Mass : [(M+H) + ] : 977

[0340]

[0341] [Synthesization Example 8] Synthesis of Compound 34

[0342]

[0343] Compound 34 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 47.6 mmol) of Core 4 (Preparation Example 4), 29.3 g (1.0 eq, 47.6 mmol) of [1,1'-biphenyl]-2-yl([1,1'-biphenyl]-4-yl)(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.8 g (2.4 mmol) of Pd(PPh3), and 13.2 g (95.2 mmol) of K2CO3 were used with 800 ml of THF and 200 ml of H2O, respectively, to obtain 23.4 g (yield 50.3%) of compound 34.

[0344] Mass : [(M+H) + ] : 977

[0345]

[0346] [Synthesization Example 9] Synthesis of Compound 38

[0347]

[0348] Compound 38 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Core 3 of [Preparation Example 3], 31.5 g (1.2 eq, 45.6 mmol) of tri([1,1'-biphenyl]-4-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 21.4 g (yield 53.5%) of compound 38.

[0349] Mass : [(M+H) + ] : 1053

[0350]

[0351] [Synthesization Example 10] Synthesis of Compound 47

[0352]

[0353] Compound 47 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Compound 1 of [Preparation Example 1], 24.6 g (1.2 eq, 45.6 mmol) of [1,1'-biphenyl]-4-yldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 17.4 g (yield 50.7%) of Compound 47.

[0354] Mass : [(M+H) + ] : 901

[0355]

[0356] [Synthesization Example 11] Synthesis of Compound 53

[0357]

[0358] Compound 53 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.1 mmol) of Core 2 of [Preparation Example 2], 23.4 g (1.0 eq, 38.1 mmol) of [1,1':3',1''-terphenyl]-4'-yldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.2 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 16.1 g (yield 43.2%) of compound 53.

[0359] Mass : [(M+H) + ] : 977

[0360]

[0361] [Synthesization Example 12] Synthesis of Compound 63

[0362]

[0363] Compound 63 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Core 1 of [Preparation Example 1], 31.5 g (1.2 eq, 45.6 mmol) of di([1,1'-biphenyl]-3-yl)([1,1'-biphenyl]-4-yl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 22.2 g (yield 55.5%) of compound 63.

[0364] Mass : [(M+H) + ] : 1053

[0365]

[0366] [Synthesization Example 13] Synthesis of Compound 71

[0367]

[0368] Compound 71 was prepared in the same manner as in Synthesis Example 1, except that 20.0 g (1 eq, 38.0 mmol) of Core 3 of [Preparation Example 3], 24.6 g (1.2 eq, 45.6 mmol) of [1,1'-biphenyl]-3-yldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.2 g (1.9 mmol) of Pd(PPh3), and 10.5 g (76.0 mmol) of K2CO3 were mixed with 800 ml of THF and 200 ml of H2O, respectively, to obtain 17.1 g (yield 49.8%) of compound 71.

[0369] Mass : [(M+H) + ] : 901

[0370]

[0371] [Synthesization Example 14] Synthesis of Compound 90

[0372]

[0373] Compound 4 of [Preparation Example 4] 20.0 g (1 eq, 38.1 mmol), tri([1,1'-biphenyl]-2-yl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane 26.3 g (1.0 eq, 38.1 mmol), Pd(PPh3) 42.2 g (1.9 mmol), and K2CO3 10.5 g (76.2 mmol) were prepared in the same manner as in Synthesis Example 1, except that 800 ml of THF and 200 ml of H2O were used, respectively, to obtain 15.0 g (yield 37.5%) of compound 90.

[0374] Mass : [(M+H) + ] : 1053

[0375]

[0376] [Synthesization Example 15] Synthesis of Compound 94

[0377]

[0378] Compound 94 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Compound Core 5 of [Preparation Example 5], 30.7 g (1.2 eq, 57.0 mmol) of [1,1'-biphenyl]-3-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 19.4 g (yield 45.3%).

[0379] Mass : [(M+H) + ] : 901

[0380]

[0381] [Synthesization Example 16] Synthesis of Compound 96

[0382]

[0383] Compound 96 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Core 5 of [Preparation Example 5], 35.0 g (1.2 eq, 57.0 mmol) of [1,1':2',1''-terphenyl]-4'-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 18.9 g (yield 40.7%) of compound 96.

[0384] Mass : [(M+H) + ] : 977

[0385]

[0386] [Synthesization Example 17] Synthesis of Compound 97

[0387]

[0388] Compound 97 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 45.4 mmol) of Core 6 (Preparation Example 6), 33.5 g (1.2 eq, 54.4 mmol) of [1,1':3',1''-terphenyl]-5'-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.6 g (2.3 mmol) of Pd(PPh3), and 12.5 g (90.7 mmol) of K2CO3 were used with 200 ml of THF and 50 ml of H2O, respectively, to obtain 30.2 g (yield 66.3%) of compound 97.

[0389] Mass : [(M+H) +] : 1002

[0390]

[0391] [Synthesization Example 18] Synthesis of Compound 107

[0392]

[0393] Compound 107 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 45.4 mmol) of Core 6 of [Preparation Example 6], 37.6 g (1.2 eq, 54.4 mmol) of tri([1,1'-biphenyl]-4-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) silane, 42.6 g (2.3 mmol) of Pd(PPh3), and 12.5 g (90.7 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 29.2 g (yield 59.7%) of compound 107.

[0394] Mass : [(M+H) + ] : 1078

[0395]

[0396] [Synthesization Example 19] Synthesis of Compound 116

[0397]

[0398] Compound 116 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Core 5 of [Preparation Example 5], 30.8 g (1.2 eq, 57.0 mmol) of 2-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)pyridine), 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 21.8 g (yield 50.7%) of compound 116.

[0399] Mass : [(M+H)+ ] : 902

[0400]

[0401] [Synthesization Example 20] Synthesis of Compound 117

[0402]

[0403] Compound 117 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Core 3 (Preparation Example 3), 43.9 g (1.2 eq, 57.0 mmol) of 2-(3'-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 25.5 g (yield 47.4%) of compound 117.

[0404] Mass : [(M+H) + ] : 1132

[0405]

[0406] [Synthesization Example 21] Synthesis of Compound 121

[0407]

[0408] Compound 121 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Compound 1 of [Preparation Example 1], 4-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,6-diphenylpyrimidine (39.5 g (1.2 eq, 57.0 mmol), Pd(PPh3) (42.7 g (2.4 mmol)), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 21.7 g (yield 43.3%) of Compound 121.

[0409] Mass : [(M+H) + ] : 1055

[0410]

[0411] [Synthesization Example 22] Synthesis of Compound 140

[0412]

[0413] Compound 140 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 40.6 mmol) of Compound Core 7 of [Preparation Example 7], 26.2 g (1.2 eq, 48.7 mmol) of [1,1'-biphenyl]-3-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.3 g (2.0 mmol) of Pd(PPh3), and 11.2 g (81.1 mmol) of K2CO3 were used with 200 ml of THF and 50 ml of H2O, respectively, to obtain 25.4 g (yield 63.0%).

[0414] Mass : [(M+H) + ] : 991

[0415]

[0416] [Synthesization Example 23] Synthesis of Compound 143

[0417]

[0418] Compound 143 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 41.5 mmol) of Core 8 (Preparation Example 8), 26.8 g (1.2 eq, 49.8 mmol) of [1,1'-biphenyl]-3-yldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.4 g (2.1 mmol) of Pd(PPh3), and 11.5 g (83.0 mmol) of K2CO3 were used with 200 ml of THF and 50 ml of H2O, respectively, to obtain 26.7 g (yield 65.8%) of compound 143.

[0419] Mass : [(M+H) + ] : 977

[0420]

[0421] [Synthesization Example 24] Synthesis of Compound 147

[0422]

[0423] Compound 147 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 41.5 mmol) of Core 9 of [Preparation Example 9], 26.8 g (1.2 eq, 49.8 mmol) of [1,1'-biphenyl]-2-yldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.4 g (2.1 mmol) of Pd(PPh3), and 11.5 g (83.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 25.6 g (yield 63.1%) of compound 147.

[0424] Mass : [(M+H) + ] : 977

[0425]

[0426] [Synthesization Example 25] Synthesis of Compound 152

[0427]

[0428] Compound 152 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 41.5 mmol) of Core 9 of [Preparation Example 9], 30.6 g (1.2 eq, 49.8 mmol) of di([1,1'-biphenyl]-4-yl)(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.4 g (2.1 mmol) of Pd(PPh3), and 11.5 g (83.0 mmol) of K2CO3 were used with 200 ml of THF and 50 ml of H2O, respectively, to obtain 30.5 g (yield 69.8%) of compound 152.

[0429] Mass : [(M+H) + ] : 1053

[0430]

[0431] [Synthesization Example 26] Synthesis of Compound 173

[0432]

[0433] Compound 173 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Compound 1 of [Preparation Example 1], 35.0 g (1.2 eq, 57.0 mmol) of [1,1'-biphenyl]-4-yldiphenyl(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 23.1 g (yield 49.9%) of Compound 173.

[0434] Mass : [(M+H) + ] : 977

[0435]

[0436] [Synthesization Example 27] Synthesis of Compound 174

[0437]

[0438] Compound 174 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Compound 1 of [Preparation Example 1], 35.0 g (1.2 eq, 57.0 mmol) of [1,1'-biphenyl]-3-yldiphenyl(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 25.3 g (yield 54.4%) of Compound 174.

[0439] Mass : [(M+H) + ] : 977

[0440]

[0441] [Synthesization Example 28] Synthesis of Compound 176

[0442]

[0443] Compound 176 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Core 3 (preparation example 3), 35.0 g (1.2 eq, 57.0 mmol) of [1,1'-biphenyl]-4-yldiphenyl(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 22.4 g (yield 48.1%) of compound 176.

[0444] Mass : [(M+H) + ] : 977

[0445]

[0446] [Synthesization Example 29] Synthesis of Compound 191

[0447]

[0448] Compound 191 was prepared in the same manner as in Synthesis Example 1, except that 25.0 g (1 eq, 47.5 mmol) of Compound 1 of [Preparation Example 1], 35.0 g (1.2 eq, 57.0 mmol) of ([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 42.7 g (2.4 mmol) of Pd(PPh3), and 13.1 g (95.0 mmol) of K2CO3 were mixed with 200 ml of THF and 50 ml of H2O, respectively, to obtain 29.0 g (yield 67.4%) of Compound 191.

[0449] Mass : [(M+H) + ] : 906

[0450]

[0451] [Example 1] Fabrication of a blue organic electroluminescent device (electron transport layer)

[0452] After purifying the compound 97 synthesized in the above synthesis example to high purity using a commonly known method, a blue organic electroluminescent device was fabricated as follows.

[0453] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0454] An organic electroluminescent device was fabricated by stacking HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET-1 (50 Å) / compound 97 : LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in that order on the ITO transparent electrode prepared as above.

[0455] The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-1, and LiQ used at this time are as follows.

[0456]

[0457]

[0458] [Examples 2–5] Fabrication of Blue Organic Electroluminescent Devices

[0459] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the materials listed in Table 1 below were used instead of Compound 97, which was used as the electron transport layer material in Example 1.

[0460]

[0461] [Comparative Example 1] Fabrication of a blue organic electroluminescent device

[0462] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the following compound ET-2 was used instead of compound 97, which was used as the electron transport layer material in Example 1. The structure of the compound ET-2 used is as follows.

[0463]

[0464]

[0465] [Evaluation Example 1]

[0466] For each blue organic electroluminescent device fabricated in Examples 1 to 5 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0467] Sample Electron Transport Layer Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 1 Compound 974.5 4586.5 Example 2 Compound 1074.6 4616.3 Example 3 Compound 1164.4 4606.2 Example 4 Compound 1174.3 4596.6 Example 5 Compound 1214.2 4616.7 Comparative Example 1 ET-24.7 4606.0

[0468] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 5, which used the compound according to the present invention as an electron transport layer material, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 1, which used the compound ET-2, a conventional electron transport layer material, as the electron transport layer.

[0469] [Example 6] Fabrication of a blue organic electroluminescent device (electron transport auxiliary layer)

[0470] Compound 2 synthesized in the above synthesis example was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0471] A glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0472] An organic electroluminescent device was fabricated by stacking HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / Compound 2 (50 Å) / ET-3 : LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in that order on the ITO transparent electrode prepared as above.

[0473] The structures of HT-1, HAT-CN, HT-2, BH, BD, and LiQ used at this time are as described in Example 1, and the structure of ET-3 is as follows.

[0474]

[0475]

[0476] [Examples 7–29] Fabrication of Blue Organic Electroluminescent Devices

[0477] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 6, except that the compounds listed in Table 2 below were used instead of Compound 2, which was used as the electron transport auxiliary layer material in Example 6.

[0478]

[0479] [Comparative Examples 2–4] Preparation of Blue Organic Electroluminescent Devices

[0480] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 6, except that compounds ET-4 to ET-6 were each deposited to a thickness of 50 Å instead of compound 2, which was used as the electron transport auxiliary layer material in Example 6.

[0481] The structures of the compounds ET-4, ET-5, and ET-6 used at this time are as follows.

[0482]

[0483]

[0484] [Evaluation Example 2]

[0485] For the organic electroluminescent devices prepared in Examples 6 to 29 and Comparative Examples 2 to 4, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0486] Sample Electron Transport Assisted Layer Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 6 Compound 24.34616.6 Example 7 Compound 54.04606.5 Example 8 Compound 124.14606.6 Example 9 Compound 184.24616.9 Example 10 Compound 234.24616.8 Example 11 Compound 274.34626.9 Example 12 Compound 324.44597.0 Example 13 Compound 344.04597.1 Example 14 Compound 384.14586.6 Example 15 Compound 474.24626.8 Example 16 Compound 534.14607.2 Example 17 Compound 633.84636.8 Example 18 Compound 714.44586.7 Example 19 Compound 903.94616.9 Example 20 Compound 944.24606.4 Example 21 Compound 964.34606.6 Example 22 Compound 1404.14597.0 Example 23 Compound 1434.04606.5 Example 24 Compound 1473.94606.4 Example 25 Compound 1524.34626.5 Example 26 Compound 1734.54607.1 Example 27 Compound 1744.24606.5 Example 28 Compound 1764.44616.7 Example 29 Compound 1914.04606.9 Comparative Example 2ET-44.84606.0 Comparative Example 3ET-54.74616.2 Comparative Example 4ET-64.64606.1

[0487] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 6 to 29, which include the compound according to the present invention as an electron transport auxiliary layer material, exhibited superior performance in terms of current efficiency and driving voltage compared to the organic electroluminescent devices of Comparative Examples 2 to 4.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A plurality of Xs are identical or different from one another, and each is independently CR5 or N, provided that at least two of the plurality of Xs are N, Ar1 consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, However, if Ar1 is a carbazole group, a structure in which the N of the carbazole group is directly bonded to the X-containing ring is excluded, and L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei, m and n are each independently integers from 0 to 3, and R1 to R4 are identical or different from each other, and each independently C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group; R5 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei; a to c are each independently integers from 0 to 5, and h is an integer from 0 to 4, provided that a+b+c+h ≥ 1, and R 11 to R 14 The elements are identical or different from each other and are each independently selected from the group consisting of deuterium (D), halogen, and cyano group, and d is an integer from 0 to 4, and e to g are each independently integers from 0 to 5, and The arylene group and heteroarylene group of L1 to L2 above; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group of Ar1 and R5 above; The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of the above R1~R4 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

2. In Paragraph 1, The above X-containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates the part connected to the above chemical formula 1, and Ar1 is as defined in Paragraph 1.

3. In Paragraph 1, Ar1 is C1~C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 It is selected from the group consisting of arylsilyl groups, and The alkyl group, aryl group, heteroaryl group, and arylsilyl group of the above Ar1 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

4. In Paragraph 1, Ar1 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 21 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

5. In Paragraph 1, L1 and L2 are each independently single bonds, or compounds selected from any one of the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 23 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

6. In Paragraph 1, R1 to R4 are identical or different from each other, and each independently C1 to C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound that forms a condensation ring by combining with any adjacent group selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

7. In Paragraph 1, A compound in which at least one of R1 to R4 that does not form a condensation ring has a substituent selected from any one of the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 22 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

8. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above formula, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1.

9. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 6 to 12: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] In the above formula, X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1, provided that cases where a to c and h are each 0 are excluded.

10. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 13 to 18: [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] In the above formula, X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1.

11. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 19 to 27: [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] In the above formula, X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and Y1 and Y2 are identical or different from each other, and each independently O, S, NR 31 , and CR 32 R 33 It is selected from a group consisting of, R 31 to R 33 They are identical or different from each other, and each independently hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, Rings A1 and A2 are identical or different from each other and are each independently condensed polycyclic aromatic rings having 8 to 18 carbon atoms.

12. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 28 to 30: [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] In the above formula, X, Ar1, R 2~ R4, R 11 ~R 14 , b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and Ring B is a condensed aromatic ring of monocyclic or polycyclic form having 6 to 18 carbon atoms, and Ring C is a cycloalkyl group or an adamantane group having 3 to 12 carbon atoms, and Z is O, S, NR 31 , and CR 32 R 33 It is selected from a group composed of, R 31 to R 33 Each independently consists of hydrogen, deuterium, and C1~C 20 alkyl group of, C6~C 20 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 20 nuclei.

13. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 192.

14. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound that is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

15. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound described in any one of claims 1 to 13.

16. In Paragraph 15, An organic electroluminescent device in which the organic layer containing the above compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer.

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